Brattleboro, VT Homes

• 

  

  

  /60

  $625,000 Sold Oct 03, 2025

  • 2,731 Sq Ft
  • $229/SF
  • 65 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1880

  49 Tyler St, Brattleboro, VT 05301

  Rare opportunity to own this iconic Queen-Anne Victorian in Brattleboro’s coveted Tyler Street neighborhood. A remarkable and extremely rare blend of country and in-town living. Extraordinary and stunning views of the Connecticut River & Mount Wantastiquet. Lovingly cared for by the same owner for the past 29 yrs. This home sits proudly on the expansive 0.85-acre corner lot, in the core of

  Karen Hoppe Berkley & Veller Greenwood Country

  49 Tyler St, Brattleboro, VT 05301
• 

  

  

  /34

  Est $592,864 Not Listed For Sale

  • 2 Beds
  • 3 Baths
  • 2,500 Sq Ft

  1245 Black Mountain Rd, Brattleboro, VT 05301

  1245 Black Mountain Rd, Brattleboro, VT 05301
• 

  

  

  /27

  $425,000 Under Contract

  • 3 Beds
  • 1.5 Baths
  • 1,846 Sq Ft

  16 Vermont Ave, Brattleboro, VT 05301

  Vermont Avenue Gem! This stunning in-town Craftsman-style home is ideally located in a highly sought-after neighborhood. Just a short 1/4 mile to downtown, or in the opposite direction, the Marina and trails await. Boasting three bedrooms and 1.5 bathrooms, this home exudes charm with its exquisite woodwork, beautiful floors, and custom-built-ins throughout. Enjoy the abundance of natural light

  Thomas Dahlin Berkley & Veller Greenwood Country

  16 Vermont Ave, Brattleboro, VT 05301
• 

  

  

  /42

  $925,000 Sold Oct 01, 2025

  • 4,150 Sq Ft
  • $223/SF
  • 5 Days On Market

  • 5 Beds
  • 4.5 Baths
  • Built 1983

  65 Hillwinds N, Brattleboro, VT 05301

  This beautiful Colonial blends timeless design with contemporary enhancements. Set on over 2 acres of landscaped grounds, the property offers a country setting just minutes from Brattleboro. Inside, the floor plan has been expanded with large, light-filled rooms & custom features. The gourmet kitchen is a showstopper, w/Quartz counters, custom cabinetry, top-tier appliances, glass tile backsplash

  Robert Doyle Berkley & Veller Greenwood Country

  65 Hillwinds N, Brattleboro, VT 05301
• 

  

  

  /22

  Est $299,794 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 864 Sq Ft

  1075 Middle Rd, Brattleboro, VT 05301

  1075 Middle Rd, Brattleboro, VT 05301
• 

  

  /47

  $499,000 Under Contract

  • 4 Beds
  • 4 Baths
  • 2,372 Sq Ft

  187 Hillwinds Rd, Brattleboro, VT 05301

  Welcome home! The four bedroom home with dedicated office space is located in one of the area’s most desirable communities. Just minutes from Brattleboro, it offers the perfect blend of convenience, comfort, and outdoor living, with walking trails right nearby. The bright, open layout is ideal for everyday living and entertaining, featuring a welcoming kitchen, dining, and living area. A private

  Claire Renaud Berkley & Veller Greenwood Country

  187 Hillwinds Rd, Brattleboro, VT 05301
• 

  

  /50

  $560,000 Sold Sep 30, 2025

  • 1,658 Sq Ft
  • $338/SF
  • 5 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1988

  5134 Vermont 9, Brattleboro, VT 05301

  Escape to this hidden gem with mountain views, 17 rolling acres,& featuring a rare blend of privacy, beauty, & income potential in the heart of southern Vermont. The contemporary main house offers clean lines, warm wood floors, & modern comforts, ideal for year-round living or a peaceful retreat. Expansive windows fill the rooms with natural light & frame the stunning surroundings. This 4

  Tamara Purcell Berkley & Veller Greenwood Country

  5134 Vermont 9, Brattleboro, VT 05301
• 

  

  /12

  Est $218,500 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 924 Sq Ft

  129 West St, Brattleboro, VT 05301

  129 West St, Brattleboro, VT 05301
• 

  

  /32

  $425,000 Under Contract

  • 3 Beds
  • 1.5 Baths
  • 1,655 Sq Ft

  155 Upper Dummerston Rd, Brattleboro, VT 05301

  Great location! This 3-bedroom Colonial, built in 1920 (when houses were well-built) on Upper Dummerston Road is up the road from the Brattleboro Country Club and its golf course, cross country skiing, trails, and the West River. On a comfortable 0.75 level acres, this property is private but only 10 minutes from the center of town. Lots of windows bring in lots of light. Generous living room,

  John Hatton Berkley & Veller Greenwood Country

  155 Upper Dummerston Rd, Brattleboro, VT 05301
• 

  

  /23

  $266,000 Sold Sep 30, 2025

  • 864 Sq Ft
  • $308/SF
  • 8 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1942

  45 Blakeslee St, Brattleboro, VT 05301

  Charming Sun-Filled Cape on Corner Lot.This sweet and practical 2-bedroom, 2-bathroom Cape offers timeless appeal and everyday comfort on a sunny corner lot. Built in 1942, the home retains its original charm with 3-over-1 windows, built-ins throughout, and even a vintage ironing board cabinet. Inside, enjoy wood floors, a spacious eat-in kitchen with generous counter space, and a bright

  Liz LaVorgna Berkley & Veller Greenwood Country

  45 Blakeslee St, Brattleboro, VT 05301
• 

  

  /40

  Est $368,473 Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 1,716 Sq Ft

  36 Goldfinch Ln, Brattleboro, VT 05301

  36 Goldfinch Ln, Brattleboro, VT 05301
• 

  

  /60

  $499,000 Under Contract

  • 3 Beds
  • 2.5 Baths
  • 3,415 Sq Ft

  23 Meeting House Ln, Brattleboro, VT 05301

  First Time on the Market – Premier Brattleboro Location!Nestled on one of the most desirable lots in one of Brattleboro’s finest neighborhoods, this well-maintained home is being offered for sale for the very first time! Custom-built by the current owner in 1970 with attention to detail, this spacious ranch offers comfort, functionality, and an impressive list of amenities.Perfect for

  Bert Inman RE/MAX Town & Country

  23 Meeting House Ln, Brattleboro, VT 05301
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  /54

  $1,743,600 Sold Sep 30, 2025

  • 8,718 Sq Ft
  • $200/SF
  • 274 Days On Market

  • 7 Beds
  • 7.5 Baths
  • Built 2005

  1324 Middle Rd, Brattleboro, VT 05301

  Truly a rare and remarkable property. This custom home was lovingly designed and constructed in 2005 with a clear vision for bringing the Vermont scenery in, while maintaining the rustic charm befitting a country estate. The main house features gorgeous exposed timber frame construction throughout, natural wood flooring, paneling, and trim, extensive artisan stonework inside and out, including 3

  Adam Palmiter Berkley & Veller Greenwood/Dover

  1324 Middle Rd, Brattleboro, VT 05301
• 

  

  /32

  Est $317,910 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,008 Sq Ft

  499 S Main St, Brattleboro, VT 05301

  499 S Main St, Brattleboro, VT 05301
• 

  

  /8

  $52,000

  • Land
  • 6.1 Acres
  • $8,525 per Acre

  0 Cooke Rd, Brattleboro, VT 05301

  Amidst rolling VT farmland, sits these 6 acres in West Brattleboro. While there is road frontage on Rte 9, the driveway is off the class 4 section of Cooke Rd. There's about 250 feet of Cooke Rd that you would need to maintain before the town road. The ROW into the land parallels the power lines, which you cannot see when you're on the land. There a nice cleared shelf when you walk in and then

  Victoria Woods Brattleboro Area Realty

  0 Cooke Rd, Brattleboro, VT 05301
• 

  

  /50

  $659,000 Sold Sep 29, 2025

  • 1,600 Sq Ft
  • $412/SF
  • 4 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2018

  86 Stark Rd, Brattleboro, VT 05301

  This property is a fine example of a labor of love by it's owner; he built everything from the literal ground, up. There are 3 bedrooms and 2 full baths, including a primary bedroom with ensuite, as well as a loft and a massive bonus room. You'll congregate around the granite countertops while cooking amidst the cathedral ceiling and fireplace ambiance. There's an abundance of things to love

  Victoria Woods Brattleboro Area Realty

  86 Stark Rd, Brattleboro, VT 05301
• 

  

  /27

  Est $248,614 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,665 Sq Ft

  379 S Main St, Brattleboro, VT 05301

  379 S Main St, Brattleboro, VT 05301
• 

  

  /17

  $209,000

  • 1 Bed
  • 1 Bath
  • 720 Sq Ft

  75 Mather Rd, Brattleboro, VT 05301

  Great Location, Great opportunity! Currently, a 1-bedroom, 1-bath home sits back on a desirable, pleasant country road. It is a larger lot than most, and with vision, here is an opportunity to start home ownership, downsize to a one-level with efficient living space. Use an investment or create your small Vermont getaway. This sweet spot is ready for your vision and ideas. This property is in

  Kristen Ziter Taylor Brattleboro Area Realty

  75 Mather Rd, Brattleboro, VT 05301
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  /34

  $310,000 Sold Sep 26, 2025

  • 1,025 Sq Ft
  • $302/SF
  • 8 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1972

  35 Hillcrest Terrace, Brattleboro, VT 05301

  Open House August 1, 5:30-7:00 and August 2, 10-11:30. Welcome to 35 Hillcrest Terrace, a well-loved home owned by the same family for over 20 years, perfectly situated in one of Brattleboro’s most convenient neighborhoods. Just moments from Memorial Park, this charming property offers easy access to recreation, walking trails, and town amenities while providing a peaceful, residential

  Morriah Adams BHG Masiello Brattleboro

  35 Hillcrest Terrace, Brattleboro, VT 05301
• 

  

  /23

  Est $298,684 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,539 Sq Ft

  380 S Main St, Brattleboro, VT 05301

  380 S Main St, Brattleboro, VT 05301
• 

  

  /19

  $190,000

  • 2 Beds
  • 1 Bath
  • 930 Sq Ft

  39 Brookside Dr Unit 3, Brattleboro, VT 05301

  Desirable 2 bedroom, 1 bath low maintenance, affordable home. Your spacious living/dining area has sliders looking out to the woods and a small yard space. Upstairs are 2 large bedrooms and a full bath. The lower level is a 465 square foot basement for extra storage with washer/dryer hookup. The entire interior has been freshly painted, new kitchen cabinets, countertop, new flooring, new bathroom

  Angela Sherman Brattleboro Area Realty

  39 Brookside Dr Unit 3, Brattleboro, VT 05301
• 

  

  /27

  $470,000 Sold Sep 26, 2025

  • 3,148 Sq Ft
  • $149/SF
  • 49 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1919

  672 E Orchard St, West Brattleboro, VT 05301

  You can't beat this location, overlooking the Brattleboro Country Club golf course. This home was built circa 1919, and has many cool vintage features such as retro curved metal kitchen cabinets and baths. Generous rooms include a large living room with two field-stone fireplaces, a spacious family room. This is a 3 bedroom house with 3 full bathrooms, but it's really about how you configure

  John Hatton Berkley & Veller Greenwood Country

  672 E Orchard St, West Brattleboro, VT 05301
• 

  

  /12

  Est $356,783 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,840 Sq Ft

  71 Home St, Brattleboro, VT 05301

  71 Home St, Brattleboro, VT 05301
• 

  

  /24

  $29,900

  • 2 Beds
  • 1 Bath
  • 684 Sq Ft

  97 Glen St, Brattleboro, VT 05301

  Finally!! Affordable!! This just right sized home is tucked into the 55 and older park for peace and quiet. Along the brook, the damaged homes have been removed and replaced with open green space with a gentle park like feel. There is an awning over the stairs, an added pitched roof, spacious front end kitchen/dining with several windows and some built-ins. Located in one of the 3 parks, making

  Angela Sherman Brattleboro Area Realty

  97 Glen St, Brattleboro, VT 05301
• 

  

  /47

  $305,000 Sold Sep 23, 2025

  • 1,222 Sq Ft
  • $250/SF
  • 49 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1942

  1082 W River Rd, Brattleboro, VT 05301

  Welcome to 1082 West River Road — a peaceful, well-located gem just minutes from downtown Brattleboro. This charming home offers the perfect blend of convenience, outdoor space, and natural beauty. Set on a spacious lot with a large, open yard, there's room to garden, gather, or simply relax and enjoy the Vermont seasons. The private river access makes it easy to enjoy kayaking, swimming, or

  Kate Barry EXP Realty

  1082 W River Rd, Brattleboro, VT 05301
• 

  

  /16

  Est $385,748 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,722 Sq Ft

  68 Wilsons Woods Rd, Brattleboro, VT 05301

  68 Wilsons Woods Rd, Brattleboro, VT 05301
• 

  

  /54

  $1,400,000

  • 5 Beds
  • 4.5 Baths
  • 4,908 Sq Ft

  131 Stark Rd, Brattleboro, VT 05301

  Remember when you were 6 and the Hundred Acre Wood seemed as big as the whole world? Now is the time to write your own story...and live in your own Hundred Acre Wood....only this one is grown up with 103 acres, 35 acres of open meadow, about 1/4 mile bordering the Whetstone Brook, a great barn, nearly 4000 square feet of living space and so many stories to live! With a perfect

  Christine Lewis Brattleboro Area Realty

  131 Stark Rd, Brattleboro, VT 05301
• 

  

  /29

  $322,500 Sold Sep 23, 2025

  • 1,548 Sq Ft
  • $208/SF
  • 79 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1958

  11 Maple St, Brattleboro, VT 05301

  Charming and well-built Cape-style home featuring 4 bedrooms and 2 full baths. The updated kitchen boasts tiled floors, generous counter space, and modern finishes—perfect for the home chef. Just off the kitchen, the dining room includes a sliding door that opens to the backyard and patio, ideal for indoor-outdoor entertaining.Beautiful hardwood floors run throughout the home—no carpet here.

  Monica Sumner BHG Masiello Brattleboro

  11 Maple St, Brattleboro, VT 05301
• 

  

  /40

  Est $453,634 Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 1,444 Sq Ft

  67 Wilsons Woods Rd, Brattleboro, VT 05301

  67 Wilsons Woods Rd, Brattleboro, VT 05301
• 

  

  /24

  $400,000 Open Sun 11AM - 1PM

  • 5 Beds
  • 3 Baths
  • 2,254 Sq Ft

  85 Stockwell Dr, Brattleboro, VT 05301

  Motivated Seller! Sweet! This 5 bedroom /3 bath home is located in one of our most sought after neighborhoods, is newly remodeled, has 2 pellet stoves for economical heat and a nice back deck. Lots of opportunities to garden, relax in a hammock or play with pets. Flexible floor plan is perfect for at home workers, multigenerational living and aging in place. Hop the MOOVER and take a ride

  Christine Lewis Brattleboro Area Realty

  85 Stockwell Dr, Brattleboro, VT 05301
• 

  

  /40

  $781,000 Sold Sep 19, 2025

  • 2,663 Sq Ft
  • $293/SF
  • 33 Days On Market

  • 3 Beds
  • 5 Baths
  • Built 1944

  1194 Ames Hill Rd, Brattleboro, VT 05301

  Welcome to The Appleshed. Starting as a storage structure within an old apple orchard, to a gentleman's hunting/fishing camp, to the cherished family home it is today, this property has had many lives and grown into a beloved gathering place for generations. Now it’s ready for its next chapter. Set on 63.8 acres with a babbling brook and breathtaking views of Mount Monadnock, this is a true

  Keith Nowak Four Seasons Sotheby's Int'l Realty

  1194 Ames Hill Rd, Brattleboro, VT 05301
• 

  

  /30

  Est $399,631 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,719 Sq Ft

  49 Marlboro Ave, Brattleboro, VT 05301

  49 Marlboro Ave, Brattleboro, VT 05301
• 

  

  /60

  $415,000

  • 6 Beds
  • 2 Baths
  • 2,048 Sq Ft

  58-60 Frost Place, Brattleboro, VT 05301

  Back on the market - Unit 58 is now Vacant! Located in the heart of downtown Brattleboro, Vermont's vibrant southern hub, recently dubbed "one of the best small towns in America". This turnkey income generator features two 3 bedroom units, one with a successful Airbnb rental history, completely renovated in 2018, with in-unit washer/dryer. Enter through the mudroom with generous built-in storage.

  Lily Gautot Greenwald Realty Group

  58-60 Frost Place, Brattleboro, VT 05301
• 

  

  /15

  $55,000 Sold Sep 19, 2025

  • 2,090 Sq Ft
  • $26/SF
  • 432 Days On Market

  • Built 1860

  211 High St, Brattleboro, VT 05301

  Here's a great opportunity! Formerly a 2 unit multi-family, this is currently a shell ready for your finishing! This property will need everything ... heating, electrical, plumbing, exterior work and full interior finishing. Very convenient to downtown, some off street parking but nicely sited above the road. Please do NOT park in the driveway.

  A.J. Bellville Bellville Realty

  211 High St, Brattleboro, VT 05301
• 

  

  /24

  Est $600,466 Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 1,592 Sq Ft

  89 Oak Grove Ave, Brattleboro, VT 05301

  89 Oak Grove Ave, Brattleboro, VT 05301
• 

  

  /60

  $5,900,000

  • 4 Beds
  • 8 Baths
  • 16,736 Sq Ft

  1950 Collins Rd, Brattleboro, VT 05301

  Exceptional 177+ Acre Estate with Luxury Log Home, Event Venue & Craft Beverage Facilities. Experience unmatched luxury and opportunity on this remarkable 177+ acre estate. Featuring an 8,000+ sq ft timber frame log home, a 7,100 sq ft finished event venue, and on-site winery, craft brewery, and champagne-making facilities, this turn-key property is ideal as a private residence, retreat, or

  Margretta Fischer Wohler Realty Group

  1950 Collins Rd, Brattleboro, VT 05301
• 

  

  /13

  $269,141 Sold Sep 12, 2025

  • 956 Sq Ft
  • $282/SF
  • 6 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1929

  81 Oak Grove Ave, Brattleboro, VT 05301

  Welcome to this delightful 2-bedroom, 1-bathroom bungalow nestled in one of the most sought-after neighborhoods! Brimming with character and warmth, this cozy home offers a perfect blend of vintage charm and modern convenience. Many upgrades including a garage makeover, storage shed, roof, back porch, and so much more. Step inside to find a bright, inviting living space with hardwood floors,

  Claire Renaud Berkley & Veller Greenwood Country

  81 Oak Grove Ave, Brattleboro, VT 05301
• 

  

  /14

  Est $332,989 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,492 Sq Ft

  131 Oak Grove Ave, Brattleboro, VT 05301

  131 Oak Grove Ave, Brattleboro, VT 05301
• 

  

  /30

  $369,000 Open Sat 11AM - 1PM

  • 3 Beds
  • 2 Baths
  • 1,703 Sq Ft

  1089 Marlboro Rd, Brattleboro, VT 05301

  The one you have been waiting for! This traditional New England cape with a twist checks all the boxes! Remodeled in the 90's, it has a cook's delight for a kitchen with tons of cabinets and lots of countertops for baking prep...cookies and breads are a must!. The first floor was expanded to almost double the size of the living room, adding a fireplace and a main bedroom. Aging in place is easy

  Christine Lewis Brattleboro Area Realty

  1089 Marlboro Rd, Brattleboro, VT 05301
• 

  

  /20

  $265,000 Sold Sep 12, 2025

  • 1,178 Sq Ft
  • $225/SF
  • 6 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1970

  17 Winter Ct, Brattleboro, VT 05301

  Classic Ranch Style Home! Just starting out or thinking of downsizing? This could be the one! Nestled in a sweet neighborhood, this charming ranch offers easy one-level living just minutes from downtown shopping, schools, and recreation. Set on a manageable 0.2 acre lot, this home features a bright enclosed porch/bonus room perfect for morning coffee, reading, or relaxing year-round. Continuing

  Liz LaVorgna Berkley & Veller Greenwood Country

  17 Winter Ct, Brattleboro, VT 05301

Showing Results 41 - 80, Page 2 of 18